Bisphenol

The bisphenols (/ˈbɪsfɪnɒl/) are a group of chemical compounds with two hydroxyphenyl functionalities. Most of them are based on diphenylmethane. The exceptions are bisphenol S, P, and M. "Bisphenol" is a common name; the letter following refers to one of the reactants. Bisphenol A is the most popular representative of this group, often simply called "bisphenol."[1]

List

Structural formula Name CAS Reactants Systematic name
Bisphenol A80-05-7PhenolAcetone2,2-Bis(4-hydroxyphenyl)propane
Bisphenol AP1571-75-1PhenolAcetophenone1,1-Bis(4-hydroxyphenyl)-1-phenyl-ethane
Bisphenol AF1478-61-1PhenolHexafluoroacetone2,2-Bis(4-hydroxyphenyl)hexafluoropropane
Bisphenol B77-40-7PhenolButanone2,2-Bis(4-hydroxyphenyl)butane
Bisphenol BP1844-01-5PhenolBenzophenoneBis-(4-hydroxyphenyl)diphenylmethane
Bisphenol C79-97-0CresolAcetone2,2-Bis(3-methyl-4-hydroxyphenyl)propane
Bisphenol C 214868-03-2PhenolDichloromethaneBis(4-hydroxyphenyl)-2,2-dichlorethylene
Bisphenol E2081-08-5 PhenolAcetaldehyde1,1-Bis(4-hydroxyphenyl)ethane
Bisphenol F620-92-8PhenolFormaldehydeBis(4-hydroxyphenyl)methane
Bisphenol G127-54-82-IsopropylphenolAcetone2,2-Bis(4-hydroxy-3-isopropyl-phenyl)propane
Bisphenol M13595-25-01,3-Bis(2-(4-hydroxyphenyl)-2-propyl)benzene
Bisphenol S80-09-1PhenolSulfur trioxideBis(4-hydroxyphenyl)sulfone
Bisphenol P2167-51-31,4-Bis(2-(4-hydroxyphenyl)-2-propyl)benzene
Bisphenol PH24038-68-42-PhenylphenolAcetone5,5’ -(1-Methylethyliden)-bis[1,1’-(bisphenyl)-2-ol]propane
Bisphenol TMC129188-99-4Phenol3,3,5-Trimethylcyclohexanone1,1-Bis(4-hydroyphenyl)-3,3,5-trimethyl-cyclohexane
Bisphenol Z843-55-0PhenolCyclohexanone1,1-Bis(4-hydroxyphenyl)-cyclohexane

Bisphenol A diglycidyl ether (BADGE) is another bisphenol derivative, along with EPI-001.

Health effects

Bisphenols A (BPA) and S (BPS) have been shown to be endocrine disruptors.[2][3] Due to its high production volumes BPA has been characterised as a "pseudo-persistent" chemical,[4] leading to its spreading and potential accumulation in a variety of environmental matrices.

Prevention measures

These products tend to release from the material when heated; as a precaution, it is recommended for the consumer:

  • not to heat food in a plastic packaging in a microwave oven, or a tin can (its inside coating is often epoxy) with a bain-marie;
  • use a pitcher material other than plastic, not a plastic bottle.

References

  1. Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus (2002). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313..
  2. "BPA-Free Plastic Containers May Be Just as Hazardous". Scientific American. Retrieved 8 August 2015.
  3. "Bisphenol A (BPA) & Bisphenol S (BPS)". SaferChemicals.org. Retrieved 8 August 2015.
  4. Pivnenko, K.; Pedersen, G. A.; Eriksson, E.; Astrup, T. F. (2015-10-01). "Bisphenol A and its structural analogues in household waste paper". Waste Management. 44: 39–47. doi:10.1016/j.wasman.2015.07.017. PMID 26194879.
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